History YMMV / ThatsMyBoy

* HilariousInHindsight: Creator/LeightonMeester portrays [[spoiler:an apparently quirky but actually a complete jerkoff of a bride-to-be that cheats on her husband-to-be [[BrotherSisterIncest with her brother]] ]] and in the series finale of her show, ''Series/GossipGirl'', [[spoiler:a half-brother and sister (they share a brother) get married]].
** Donny fathers Han Solo/Todd at 12 years old. Creator/AdamSandler actually is 12 years older than Creator/AndySamberg in RealLife.

** Rex Ryan is a New Englands Patriots fan. In real-life, he coached two of the Pats' division rivals in the Buffalo Bills and the '''[[ArchEnemy New York Jets]]'''.

* VindicatedByHistory: The negative reception of the film has cooled down over the years and nowadays, there's no shortage of people on social media platforms like Twitter and YouTube that admit to liking the movie and finding it funny.

* TheWoobie: Todd. He grew up neglected by his father. He only knew his mother by visiting her in prison. He's a diabetic due to his father's neglectful parenting. His fiancée is cheating on him [[ReallyGetsAround with many people]] [[spoiler:including her ''younger brother'']] and only marrying him [[GoldDigger because of his money]], and his dad only shows up just to ask him for money to pay for the IRS instead of actually spending quality time with him.

* WTHCastingAgency: Creator/JamesCaan and Creator/SusanSarandon, most especially. Creator/AndySamberg also counts, as he was cast to play a fairly generic OnlySaneMan despite being famous for playing [[LargeHam over the top]] characters so well.

** A Ephebophile 22-year-old teacher statutory seducing her 12-year-old student.

* AcceptableTargets: The film pokes fun at former Hollywood child stars (Donny Berger who became famous simply for banging his teacher), one-hit-wonder rappers (Vanilla Ice), WASP's (Jamie Martin's upperclass privileged family), golddiggers, teachers, ephebophiles, age-gap romances, phony veterans, etc.